


Valentine's Day: Sharing the Love

by Always_Bottom_Derek



Category: Teen Wolf (TV)
Genre: Anal Fingering, Anal Sex, Bottom Derek Hale, Come Eating, Dirty Talk, Dom/sub Undertones, Dominant Stiles Stilinski, First Time Blow Jobs, Kissing, Loss of Virginity, M/M, NSFW Image in Chapter One, Power Bottom Stiles Stilinski, Prostate Massage, Rimming, Safe Sane and Consensual, Threesome - M/M/M, Top Derek Hale/Bottom Stiles Stilinski, Waxed, but not usually, dirty valentine, pillow humping, shaved, submissive Derek Hale, tit worship
Language: English
Status: Completed
Published: 2021-02-16
Updated: 2021-02-16
Packaged: 2021-03-17 21:13:43
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 6
Words: 7,629
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29478249
Author URL: https://archiveofourown.org/users/Always_Bottom_Derek/pseuds/Always_Bottom_Derek
Summary: PROMPT:Valentine’s Day prompt - Derek and Stiles’ chubby, average waiter from their Valentine’s Day date makes an offhand comment about being alone for the day. They take pity and invite him to their place for for Valentine’s Day sex. Stiles directing the guy on how to fuck Derek. Derek giving it his all and trying to make it a night to remember for the guy.Maybe you can have the waiter take a selfie while fucking Derek? Stiles gives the ok. To send to his friends as proof. Like, “Fuckers I’m getting laid on Valentine’s Day!”
Relationships: Derek Hale/Stiles Stilinski, Derek Hale/Stiles Stilinski/Original Male Character(s)
Comments: 22
Kudos: 73





	1. THE SET UP

**Author's Note:**

  * For [IcyCryos](https://archiveofourown.org/users/IcyCryos/gifts).



> My thanks to IcyCryos for this prompt and keeping after me to write until it was finished. And for all the ideas and bits of text he shared in this collaboration.
> 
> And dedicated to my own valentine Benn_Xavier.

**Summary for the Chapter:**

> Derek and Stiles start their Valentine's Day date.

**Notes for the Chapter:**

> So this was originally intended to be a two page drabble-ish piece for Valentine's Day that turned in to 23 pages of ribald smut. 
> 
> Happy late V-day folks!

**PROMPT:**

Valentine’s Day prompt - Derek and Stiles’s chubby, average waiter from their Valentine’s Day date makes an offhand comment about being alone for the day. They take pity and invite him to their place for for Valentine’s Day sex. Stiles directing the guy on how to fuck Derek. Derek giving it his all and trying to make it a night to remember for the guy.

Maybe you can have the waiter take a selfie while fucking Derek? Stiles gives the ok. To send to his friends as proof. Like, “fuckers I’m getting laid on Valentine’s Day !”

* * *

Derek exited Target, frustrated, despite the box of chocolates and the little wolf stuffie he’d bought. Thirty minutes reading through all the greeting cards and he hadn’t found anything to capture his desired sentiment for Stiles in a Valentine.

He was just about back to his car when inspiration struck. He noticed a woman carrying a bunch of heart-shaped mylar balloons. Not normally the most creative guy, the rounded curve of them with the mylar’s wrinkles gave him an immediate, naughty association.

Parked toward the back of the lot where there were fewer people, it seemed safe enough. Gifts set in the passenger seat, his fingers went to his belt. His heart pounded as he shoved the waistband of his shorts down under his junk in the open “V” of his jeans. It felt so wicked, sitting in his car, out in public, with all kinds of people milling about innocently running their errands.

Derek grimaced at the ache as he pulled his hairless ball sac downward, really giving it a good tug. The curves of his fat gonads stretching the skin taut was just what he was going for. Balls clenched in one hand, his other fiddled with his phone until the angle was just right. He snapped a few pics. 

He dropped his sore nuts and edited his new photos until he was satisfied. The heart shape of his scrotal valentine perfected, he added three <3 <3 <3 and hit send.

A moment later his phone pinged.

_lol. love you too. now get that fine fat ass down here so we can get our valentines celebration underway. im waiting._

* * *

At the coffee shop Derek offered his presents shyly. Stiles took them with a grin and patted the cushion of the booth’s bench seat next to him. Derek slid in.

“Thank you for these, Babe.” Stiles kissed his cheek and laughed at the uneasy blush beneath stubble. “I love them.” 

“Now how about we get started on _your_ present?” 

Stiles took the wolf stuffie and brushed its nose with Derek’s and said in a singsong voice just loud enough for the closest tables to overhear. 

“Who’s a horny-wolf? Huh? Is it Derek? Are you a horny-wolf bitch, Babe?”

“Stiles…” Derek growled. But the delicious humiliation had blood surging into his already eager cock so fast it hurt.

“Ummm… excuse me?”

Both Stiles and Derek looked up to see their clearly uncomfortable waiter. In his early twenties, most likely. Not fat, but definitely chubby. He was trying (unsuccessfully) to pull off the hipster look with his scraggly patched scruff and messy man-bun. The name embroidered on his coffee-stained apron read “Dustin.” 

Dustin’s cheeks blushed bright red as he nervously twirled his pen over his ticket pad. 

“Did you want to order something, guys?”

“I want coffee, black. And he’ll have a half mocha - half milk grande.” 

Derek’s balls hitched and he wiggled in his seat at the way Stiles had taken control already, ordering for him. This reversal of their usual roles was so hot.

“What type of milk, Sir?” Dustin looked at Derek. “Skim, two percent, almond, soy, oat?...”

“Oh, whole. My boyfriend likes heavy cream. Lots of it,” Stiles answered for him again, his expression leering. Now Derek's and Justin’s blushes matched. 

Stiles laughed at this as Dustin quickly scurried off to fill their order. His bright eyes scanned the room before turning to Derek.

“So…” He booped Derek’s nose. “According to this marvelous sniffer of yours, who here wants to fuck you?”

Ever since Stiles discovered he could do this, he asked the question most every place they went. It pumped up his ego knowing he was out with someone other people coveted. Today though, his reason for asking was different: one coveter was going to get a special Valentine’s treat. 

If they wanted it.

There were half a dozen folks, male, female and in-betweeners who started putting off aroused scents as soon as he’d entered, but one in particular had caught Derek’s attention.

“Uh… Our waiter?”

Stiles’ eyes widened, delighted. “Dustin? Really?” He watched Dustin fumbling behind the counter. “Yeah. He’s perfect.”

The wolf stuffie was whipped out again, only this time Stiles pressed its nose to the bulge at Derek’s crotch. “Oooooh… Someone’s excited, isn’t he?! Is this eager bitch ready to get bred?”

He laughed loudly when Derek scowled and batted the stuffie away even as his jeans pulsed visibly tighter.

When Dustin returned to the table bearing their drinks Stiles stopped him before he moved to the next table.

“Thanks, man… er, Dustin.” He made a show of pretending to read his name as if he hadn’t noticed it before. “And happy Valentine’s Day.”

The look on Dustin’s face indicated he thought there was very little to be happy about.

“So, do you have hot plans with your sweetie tonight? Doing anything special?” Stiles offered as Dustin shook his head in the negative, “Because my boyfriend Derek and I are kind of making a whole day of it.”

When this brought a sad frown to Dustin’s face, Stiles kept talking.

“Uh, hey. Please don’t take this the wrong way. I’m not trying to sexually harass you or anything… but Der and I were kind of wondering... Are you gay?”

Clearly taken aback by the question, it looked for a moment like Dustin might screech for his manager. But then he seemed to decide the better of it.

“Pansexual,” he said primly.

“Cool, cool, cool... “ Stiles offered his most winning smile while Derek looked on hopefully. 

“Are you poly too, by chance?”

The look on Dustin’s chubby face made it immediately clear he’d never considered his life could involve more than one intimate partner simultaneously. Or maybe even one intimate partner period.

“I… uh… could be?”

“Great, man. That’s excellent. Fantastic to live in these days where folks can be so much more open, you know.”

Dustin’s man-bun bobbed as he nodded but his eyes narrowed in suspicion.

“Hey, so, I don’t know what you're doing after you get off work, but I promised my guy here a special treat today and since you indicated you don’t have any romantic entanglements at the moment... Think you might be interested in joining us?... I mean, if we appealed to you?”

They left the coffee shop twenty minutes later. Derek’s stomach was tight with anticipation. “Do you think he’ll actually come?”

“Hope so.” Stiles grinned at him. “Especially since, after all, today is all about sharing the love.”

**Notes for the Chapter:**

> Thank you for reading.


	2. THE SHARING - GETTING STARTED

**Summary for the Chapter:**

> A shift in POV to Dustin's experience and the start of his Sterek romp

Dustin stood in the front room of the loft drinking it in with stunned eyes, barely able to believe his good fortune. He was still in recovery mode from finding the address left on the receipt, along with the biggest tip in his life, had actually been valid. 

In his entire twenty-two years he never imagined he’d have one, let alone two such hot guys come onto him. And their proposition… 

Here he’d thought he’d be spending yet another Valentine’s Day after work writing Star Wars fanfiction, playing CoD, and frotting his frustrated cock to release against his favorite cum-stained pillow.

He looked at Stiles and Derek who stood off in the bedroom area in a furious whispered conversation. Or, actually, most of the whispers were Stiles’. Derek, tall, ripped, and fierce-looking, just mostly stood there, shooting him bushy-browed glances and nodding occasionally.

There was still a good chance this pair might be perverted serial killers. But at this point in his unintended, perpetual virginity, if he even managed to score a handjob or a blowie before they tortured and killed him, at the hands of two such hunks, Dustin thought he could die happy.

The lean twink, Stiles, came over leading Derek by the hand. 

“Okay. Full disclosure… We haven’t done this much before or, ever, really. But my alpha stud here, really wanted a little domination and a new experience and this power bottom,” he pointed to himself, “is only too happy to give my Babe what he needs...

“So, that said, there’s just one rule. I am in charge. What I say goes. For both of you. 

“I don’t want any argument. And if you can’t follow that you’ll be out on your ass. Got it? 

“Also, if Derek gets uncomfortable at any time, or you, for that matter, and we can’t keep a happy flow, we stop. End of story. 

“No complaints from any one.”

Dustin nodded so vigorously his man-bun almost toppled off.

“Included in this, I expect 100% honesty from you.” Stiles smirked wickedly. “And trust me when I say, I’ll know if you’re lying.”

It took a few more seconds for Dustin to commit to this agreement than the other one. “Okay…” 

“Ever fucked or been fucked by anyone before?”

Dustin knew his normally pasty cheeks must be beet red from the burn of them. “No.”

“What do you normally do to get off then?”

“Just jerk off, I guess,” Dustin said with a shrug.

“Anything else? I mean come on… a hand gets pretty boring after a while. And remember, honesty is going to get you into this ass.” Stile gave Derek’s fat, denim-clad butt a hard spank to underscore the seriousness of the situation.

“I, uh…” Though he wanted to keep staring at Derek’s perfect rump, Dustin dropped his eyes in embarrassment. “I have this Kylo Ren body pillow I hump sometimes...”

He was shocked when instead of belittling him, Stiles hummed thoughtfully. “Star Wars… Good call. I’m a fan too. We should talk later. But Kylo Ren, huh? I can see that... Big, dark, broody... 

“I think you’re going to find Derek makes a good alternative.”

“Why don’t you strip him down and see if you approve of your new waifu fuck pillow?” Stiles ran his hand up and down Derek’s arm in a manner clearly meant to be soothing. “He’s promised to be a good boy for us.”

“Uh. Okay.” Dustin stepped up. The undeniable alpha-stud energy wafting of the gorgeous man in front of him made his fingers tremble. He carefully took the hem of the tight black tee-shirt Derek wore and lifted it up. 

He was tense, like his fingers might be smacked away at any moment, but Derek remained perfectly still. Divided by a wispy line of dark hair running down the middle of his low belly perfect plates of muscle twitched as they were revealed. Otherwise, his beautifully sculpted torso was completely hairless.

Derek continued to imitate a stone, watching, eyes growing more sultry as his shirt was hitched higher.

“Do you like how he’s smooth, Dustin? I had him shave this morning. He’s normally fully furred. Like a beast.” Stiles winked at Derek and ran a hand over washboard abs. “But this way… His skin is so soft... and so sensitive.”

“Can, uh… can I touch?”

Stiles grinned. ”Absolutely. Go ahead. Run your hands over all that hot man-flesh, Guy. It’s all yours today.

“Derek, get that shirt the rest of the way off and pose for him.”

Silently Derek compiled. T-shirt in a heap at their feet, he set his hands behind his head. Biceps flexed, chest puffed forward. 

Chubby fingers stroked tentatively over contours Dustin knew he’d never achieve in a million years. Under his palm Derek’s skin was warm, soft and firm at the same time. 

And his tits… Dustin licked his lips at the plushness of Derek’s plump, sleek pectorals.

Stiles didn’t miss the longing look in his eyes. “You can touch here too.” He plucked at one of Derek’s nipples making the dark bud seize and Derek bite his bottom lip. 

“My boyfriend is a real titty slut.” He laughed. “If he’s pounding me missionary and taking too long to cum, all I have to do is pinch his pretty titties and he’s spilling in a minute.”

Dustin didn’t know about Derek, but he was practically ready to spill himself at the feel of the sweet hardened nipple tip between his fingers and the sound of a bitten back gasp.

There was a sharp smack that made Dustin jump when Stiles slapped Derek’s other pec. 

“Hey, sorry to startle you, man.” Stiles turned stern eyes on Derek. “What did we agree to, Der? You’re not going to be quiet today. No holding back. Dustin and I want to hear every slutty sound you can make.”

“Dustin, want to help me get him started?”

Stiles wiggled his eyebrows and then latched onto the closest nipple. Derek tipped his head back and the moan pulled from his throat made Dustin’s dick weep.

“Uh… Okay…” 

Not nearly as aggressive he held his breath and brushed his lips over a pointed tip. Derek shuddered and uttered a soft, “holy shit.”

Encouraged by this Dustin took Derek’s whole nipple into his mouth and sucked. The feel of the tight bud on his tongue had him nursing like a babe at the breast. A glance over revealed Stiles alternating between hard suckles and bites. Teasing Derek’s little nib between his teeth. Dustin followed his example and the sounds Derek made in response were the most amazing things he’d ever heard.

Growing bolder he brought his hands up and kneaded fingers into the firm flesh of Derek’s pec. An exhilarating rush of accomplishment flushed through him when Derek’s knees literally trembled under his massage.

Stiles pulled off Derek's nipple and a hand dipped down to undo his belt and open his jeans. The other wrapped around Derek’s neck and pulled him into a messy tongue-filled kiss. 

“Like that, Babe? Yeah you do… You love being the center of all this attention, don’t you? You alpha whore.” 

Derek uttered the loveliest puppish whimper at the question and gasped a “yes” into Stiles lips.

Stiles left Derek’s mouth just long enough to gently order, “Suck his other tit, Dusty… You have to sample both of them.” 

Once Derek’s tight jeans were open Stiles took one of Dustin’s hands and guided it to his bulge. His eyes bulged too at how big it felt.

“See how hard you made him?” Hand caught between Derek’s tight boxers and “V’ed” jeans, further down Dustin found the fabric soaked.

“Yeah,” Stiles nodded. “Look at how much you’ve made him leak too. Turned this alpha stud into a messy bitch in heat in just a couple minutes.”

“Can I?... I wanna see…”

“Well, then,” Stiles grinned, “Why don’t you unwrap your Valentine, Dustin?”

There was no need to ask twice. Dustin grabbed the waistband of jeans and boxers in tandem and jerked them down so roughly it made Derek hiss.

“Sorr…” He lost his apology along with the rest of his words when the prettiest nine inches of cut, porn-worthy cock popped up to greet him from a carefully manscaped bit of close-cropped thatch..

“Holy fuck!” Dustin couldn’t help himself. He dropped to his knees in front of a dick made to be worshiped. His hands shook so badly he could hardly shimmy Derek’s jeans off the rest of the way.

So hard it looked painful, the massive rod with its dark drooling tip bobbed about as Derek stepped out of his Levi’s.

“Yeah, Derek’s cock is something, isn’t it?” Stiles eyed it appreciatively. “Hey, Babe, Give Dustin here a little show. Make it dance for him.”

A beautiful blush dripped from under Derek’s stubble all the way down to mid-belly as he began to wiggle his hips. His mammoth rod swayed from side to side and once some momentum was built, it whipped around in wide lazy circles. Drops of precum flew from its dripping tip to speckle the floor.

“White boy hasn’t got much rhythm on the dancefloor but he sure knows how to shake that dick, huh?”

Dustin couldn’t bear to blink; he was so hypnotized by the movement of Derek’s personal pendulum. “Yes…” he whispered.

Stiles stopped the motion by gripping the fat shaft in one hand. He set the other gently on the back of Dustin’s bunned dome and urged him forward. “You can’t imagine how good it feels to have this monster churning your guts. And the way it tastes… How it swells in your throat, blocks your breath…”

Pulling Derek’s dick upward revealed bare, blushed balls. Incredibly full and fat but also clearly hitched high and tight with arousal. 

“Take a look at those. Hairless too. Had him wax this fat jizz sac three days ago. Normally these monsters would be cranking out cum to put inside you. But not tonight. Tonight all that alpha spunk is going to be running across Derek’s cum-guttered belly. ‘Cause the only one cumming inside will be you, Dusty.”

At a firm shaft stroke from Stiles’ hand Derek’s nads visibly jumped in their skin.

“Look how big and heavy they are. Full of baby batter. I haven’t let him touch himself or me for three days now. And he’s horny as a fucking bunny normally. 

“You know he comes so much, even though I don’t have a womb, I swear one day he’s gonna manage to knock me up.”

“Er… I…” Dustin’s voice had finally begun to return to him. “I wanna suck him?”

Stiles leisurely pumped Derek’s dick. “Oooohhh… Hear that, Der Bear?… Your alpha, Dustin, wants to suck you. What do you say? Hmmmm?...”

Derek dipped his head into the side of Stiles’ neck and nodded. 

“Oh, no, Der… You gotta use your words, remember? Ask nicely. Beg him…”

Dustin was about to protest but stopped when Derek growled lowly, “Dustin, please…. Please suck me…” 

He’d never heard such a pretty “please” uttered. And when he glanced up and saw the pure begging need in all the green intensity of Derek’s eyes, Dustin almost choked on the spit that suddenly flooded his mouth.

He couldn’t hold back. Diving in he nuzzled under Derek’s fat dick. Denuded scrotal skin felt so soft and warm on his tongue. And the smell of manly musk here was so delicious he couldn’t help audibly snuffling into Derek’s groin, trying to pull as much of it into his pheromone-starved lungs as possible. He was so loud in his sniffing above him Stiles laughed and said something odd.

“God, the way he’s going after you, it’s like he’s a wolf too…”

Dustin didn’t spend any time puzzling over the weird comment, far too eager to see if he could fit one of Derek’s fat nuggets into his mouth. 

He could. 

He hummed, pleased at his accomplishment. Above him Derek made the most precious little whines. Switching from one to the other, Dustin was going in for thirds when Stiles stopped him.

“Let’s switch the focus here…”

Stiles held Derek’s dick, squeezing just to the precipice of pain and then releasing. Hand still on the back of Dustin’s head, he dragged Derek’s fat precum spinning cockhead over his spit-slicked lips. At the press of the spongy tip, Dustin’s mouth automatically fell open. 

“Oh, yes, boys… That’s perfect. Fuck you two look so hot together.”

Stiles dropped Derek’s dick to pull off his shirt and shimmy out of his jeans. His red briefs strained with a fat bulge of his own. He gripped this and rubbed it as Dustin took up Derek’s shaft between his own hands and sucked the fat tip of Derek’s dick in between his lips.

The way the mushroomed head filled his mouth, the taste of Derek’s drippings on his virgin tongue, Dustin’s eyes rolled back into his head and his hips juddered with his cumming.

“Ack!” Dustin popped off Derek's dick, his face fifty shades of pink.

He was stunned when Derek reached down and gently cupped his jaw. “Did you just cum, Sweetheart?”

Dustin blinked at ‘sweetheart” so kindly said and felt strangely teary. He nodded miserably as Derek helped him up to his feet.

“Hey, no worries,” Stiles assured. “It happens to all of us in the beginning.”

He took one of Dustin’s hands, Derek took the other and walked him over to the bedroom. 

**Notes for the Chapter:**

> Thank you for reading.


	3. THE SHARING - SHORT & SWEETS

**Summary for the Chapter:**

> Dustin's life is like a box of chocolates. (Especially the cream filled ones.)

“I’m sure you’ll be raring to go again in a few minutes.” Stiles turned Dustin around and gave him a light push so he toppled backwards onto the mattress. “Derek, you want to help Dusty out?”

Feet still on the floor, knees bent over the edge of the mattress Dustin watched Derek sink gracefully into a kneel between his splayed thighs. Strong fingers skillfully worked his khaki work pants down over his plump butt and chubby thighs.

The front of his tighty-whities were a mess, the pouch of them sopping wet.

“Oh, god…” Dustin gasped when Derek leaned in between his bared legs and mouthed the jizz-filled cloth at his crotch. He nuzzled against his soft, sensitive spent dick, catching bits of it in his sucking.

Dustin had never seen anything so hot.

“How about we get you out of this shirt too?” Stiles had laid down beside him on the bed and plucked at the hem of his polyester work polo.

Determined fingers worked it up over a chubby belly. Dustin tensed when it reached his tits. Stiles seemed to notice and asked, “This okay?” 

Though mortified by his man-boobs Dustin nodded. 

Shirt lifted, his breasts exposed, Stiles let out a little whistle. “Hey Der, look at these beauties.” Slender fingers kneaded soft flesh. When Stiles lightly pinched a nipple Dustin moaned, suddenly understanding all Derek’s needy noises.

He saw Derek’s head pop up above his chub-rolled belly. Derek gave him a little approving smirk before ducking back down and pulling off his briefs. 

“Oh, shit, oh shit, oh shit!” Dustin chanted when Derek sucked the entirety of his still-limp dick into his mouth and began coaxing it back to life with his tongue.

Stiles grinned at this reaction. “Yeah, Derek loves sucking cock. And he’s good at it, right?”

He pulled Dustin’s shirt off over helpless arms and skated his fingertips over soft, pale skin. He leaned close studying him intently. 

“Done much kissing?”

 _Honesty,_ Dustin remembered and shook his head “no.”

“How about we change that?”

Dustin gulped as Stiles leaned in, a hand tenderly guiding his scraggily-bearded jaw. The combination of soft lips on his own and a soft but ardent mouth on his cock had his eyes rolling, lost in a tsunami of sensations.

But this wasn’t the height of it.

Stiles broke their kiss and reached over to the night table where an open box of chocolates sat. He picked one up and popped it into his mouth. His chewing was a little obnoxious but when he dipped back down and that chocolate slicked tongue slid into his mouth, Dustin thought he might have died and gone to heaven.

“Derek likes chocolate too. Should we give him a piece?” Eagerly imagining Derek’s mouth on his own Dustin nodded.

“Derek might like his chocolate delivered a little differently, however. What do you say, Dusty?” You up for it?”

Everything they’d done so far had been mind blowing so he nodded. Stiles plucked up another chocolate, pinched this between his index and middle fingers. “Get this wet for me, Dust.”

Dusty allowed Stiles to gently finger fuck his mouth until the candy and his fingers dripped slick and sticky with spit.

“Wait, what?”

Eyes popped open, Dustin got up on his elbows again when Stiles’ fingers dropped down and the wet chocolate was pressed to his previously untouched asshole.

Stiles' fingers stopped circling and he tipped his head to the side. “Want me to stop? Or would you like to know how it feels to get your ass eaten.” 

He grinned and whispered in Dustin’s ear. “Head’s up… Derek might be even better at that than he is sucking cock.”

Surrendering to this information Dustin flopped back on the bed with a huff. He began to make little moans as Stiles’ adamant digits returned to their task. Slick as his fingers were there was a stretch but no burn when the chocolate was swallowed by his asshole.

Stiles didn’t even have to encourage, the moment his hand withdrew Derek’s mouth was there in an instant. It was so filthy, wrong, sexy, amazing-feeling, Dustin’s head crashed back against the mattress swaying side to side. 

“Jesus!”

“Nope, Stiles and Derek…” Stiles’ hands lifted the back of his head and freed his hair from the wreckage of his bun. Long fingers combed through his sweat-wet, greasy hair, teased along his earlobes, down his neck.

And below him, Derek made the roughest, sexiest happy growling sounds as he continued to feast. His determined tongue had worked Dustin’s tight bud open and hungrily lapped and sucked to get at the melted sweet inside it.

Meanwhile Derek’s skilled fingers had caught Dustin’s revived dick and stroked it. Stiles’ hot mouth latched onto a puffy nipple and teased it to hardness before trading it for the other.

“Wait… Uh… I… HOLY FUCK!!!” 

Under the assault of all these mouths and fingers, Dustin’s whole body spasmed and he came again. As soon as his dick finished twitching Derek’s mouth left his ass and began licking all his jizz off his chubby belly and sucking it out of unkempt pubes.

So sensitive, he was almost in tears by the time Derek had him cleaned up to his satisfaction. Stiles petted his head and kissed the single tear away from the corner of a blue eye.

“You did so good for us, Dust. Didn’t he Derek?”

“Beautiful,” came Derek’s one word reply.

Dustin had barely stopped gasping when Stiles pulled him onto the middle of the bed, turned him on his side and curled up behind him.

“Der, go wash your mouth out and get that beginners cock ring from the toy drawer, huh?”

Derek rose from the floor beside the bed, cock still hard and ever-drooling between his thighs. He disappeared for a few minutes. While he was gone, Stiles pressed a couple biting kisses to Dustin’s sweaty, pimpled neck. 

“Now that you’ve cum a few times, you’ll last longer the next round. Of course, the cock ring will help too.” He rested a pointy chin over Dustin’s shoulder. “After all, we want Derek well-fucked, don’t we?”

All Dustin could do was nod.

**Notes for the Chapter:**

> Thank you for reading.


	4. THE SHARING - IN THE MIDDLE

**Summary for the Chapter:**

> Life offers new openings every day. Today, one of these is Derek's pretty asshole.

It was more than he could have ever imagined when Derek slid into the bed too and snuggled up on the other side of him. Derek’s big hand rubbed up his arm, down his back, he trailed teasing fingers over his thigh, pleasantly tickled his soft belly and respectfully kneaded his moobs. Under all this affectionate dominant touch, Dustin absolutely melted.

In his haze, he thought he heard Derek oddly whisper “touch starved” in a worried tone before Stiles gently shushed him.

Strong fingers tipped Dustin’s jaw toward him and Derek dipped down and caught his mouth. He tasted not like ass but mint. 

There seemed to be no oral skill (outside talking) Derek wasn’t adept at. The way he kissed was amazing: deep and long, with carefully meted out alpha energy. Dustin floated on the drug of Derek’s tongue and was shocked to find his cock stirring to life again.

“Okay fluffy-wolf,” Stiles teased. You can kiss Dusty more later. Right now I want to see that sweet ass of yours fucked.

Derek gave a good-natured huff and broke off the kissing. 

“Why don’t you show us that pretty alpha cunt of yours? Come on, be a good bitch for us.” 

Derek sat up and rolled his shoulders making his spine crack before he turned and shuffled over until he was on all fours with his ass facing them.

“Spread those cheeks for us, Der.” There was a light grunt as Derek dropped his chest to the mattress, reached back, grabbed his plump cheeks and spread them apart.

Stiles ran a finger down his smooth spread crack. “I had him shave here too. Isn’t it pretty?”

It was.

Derek’s smooth pucker was a delicious dusky pink and its furl was so tiny and tight-looking. Dustin’s dick throbbed. 

He reached forward to follow with his own finger but hesitated. Stiles grinned and grabbed his hand, setting it on the most luscious, smooth fat asscheek. “You’re his alpha tonight... So you don’t have to keep asking, Dustin, you can take. Derek will be more than happy to give everything to you. Won’t you, Babe?”

“Mmmmm” Derek hummed.

Stiles shook his head. “Dustin, you’re alpha. Why don’t you give this big-dicked bottom a little spank and tell him he - Needs. To. Use. His. Words!”

Bolstered by Stiles’s assertion he was alpha, Dustin hardly hesitated. His first smack was relatively light, however. Derek growled in a way that sounded entirely too happy and wiggled his ass. Challenging.

So Dustin smacked him again. It was such a rush seeing the skin pink beneath his palm and the jiggle of that perfect ass flesh. A couple more smacks, each a little harder, finally pulled a moan.

“Yes... “ Derek murmured.

Three more smacks turned Derek’s smooth pale butt a beautiful rosy hue.

“Yes.” Derek gasped again and a hint of whine crept into his voice now. “I’m going to give you everything, Dustin.”

Having such a rugged, handsome, big muscled man submitting to him so beautifully was the headiest aphrodisiac Dustin had ever encountered. His cock was fully hard again.

“Isn’t it great,” Stiles whispered over his shoulder as his hands slipped down to fasten the cock ring around Dustin’s balls and the base of his risen shaft. “You and Derek are going to lose your virginities together!”

“What!?”

“Yeah,” Stiles chuckled. “Can you believe as slutty as he seems, you’re only the fourth person to ever touch his sweet asshole. And you’re gonna be the first to stick their dick inside him. 

“I mean you’re actually only the second person to stick a dick in that mouth.” Stiles beamed and winked. “The other one being yours truly.

“Even I haven’t dipped my wick into that alpha cunt yet.” Ignoring the blatant stare of disbelief Dustin shot him, Stiles continued.

“You’ll be the first to fuck that fine fat ass, pump him full of cum, breed Derek like the two-dollar whore he both wants to be and is afraid of becoming.

“Does that make you feel special, Dustin? It should. Derek, tell him how special he is.”

This time it was Stiles who landed the preemptive spank.

“Just you, Dustin.” Derek growled.

“Only you. I’ve been saving myself for you and your bare-breeding dick.” There was true hunger audible in his words.

“Not even for Stiles. This hole…” Derek released a cheek and twisted his torso just enough to take Dustin's hand and guided it to his virgin pucker. 

“Your cock will have been the only cock it’s taken.” Looking over his shoulder his green eyes locked with Dustin’s blue. “You’ll have been the only one to have been in there.”

At his side, Stiles seemed to have magically conjured a bottle of lube. He popped the cap and let it drizzle, the slick gloss of it sliding down Derek’s ass crack.

“Go on,” he urged, cricking his own index finger in example. “Get in there. Feel how tight it is. 

“You’re gonna be the one to break that in.”

At the first light press of his finger ghosting over the fringe of his rim, Derek groaned. 

“Open it, D. Come on… I need something inside me.

“Stiles and I have been dreaming about this night. And you’re the special someone we wanted for this.

“Needed.”

Dustin pushed his finger forward meeting resistance.

“Push out, Der,” Stiles ordered. 

Dustin and Stiles both stared, mesmerized as Derek complied and his little bud opened. Dustin’s finger was sucked in.

It felt so hot and soft inside. Like some sort of odd wet velvet. Derek grunted and tensed but then began to slowly rock his ass back incrementally on the invading digit. Seeing his eagerness, Dustin jumped into action.

“Wow. Yeah... Open that bitch hole up,” Stiles breathed. He bent forward and sucked a quick hickey on Derek’s shoulder. It was gone by the time he returned to staring as Derek’s ass taking Dustin’s fucking finger. "He wants more, Don't you, Babe.

“Add another.”

Dustin followed Stiles’ urging.

“Oh god…” Derek gasped.

“Look at that! You found his prostate!” 

Derek’s mammoth cock hung down between his spread thighs drooling even more heavily than before. With each side of fingers in it twitched and spurted a bit.

“How’s that feel?” 

Stiles grinned that it was Dustin who asked the question and not him.

“Good,” Derek exhaled on a shaky breath. “Amazing…”

“Okay!” Stiles had grown impatient. “Let’s get both you guys fucked!”

**Notes for the Chapter:**

> Thank you for reading...


	5. THE SHARING - IN THE END

**Summary for the Chapter:**

> Dustin loses his virginity... So does Derek.

Dustin pulled his fingers from Derek’s hole. They glistened with lube and ass juice. He followed Stiles’ prompting and positioned himself on his back, upper torso propped up on pillows at the head of the bed.

“Okay, Der. Climb on.” 

Stiles held Dustin’s dick while Derek moved over to straddle dimpled thighs. Stiles bent over on all fours and peered up at Derek’s asshole. “Sweet little baby-gape you’re sporting there, Babe. 

“Once it’s really fucked wide I’m going to pry it open with both my thumbs and look at your pretty innards.”

Derek’s dick twitched at these words and cast a string of fluid over the trembling pale paunch of Dustin’s belly. Dustin could barely breathe when Derek locked eyes with him as his hips lowered. He jumped to feel Stiles suddenly grab ahold of his dick without warning.

“Yesh!” Stiles crowed. He held Dustin’s cock and worked its sensitive tip up and down over Derek's loosened pucker before gripping it just behind the glans and slowly pressing his leaking cockhead into Derek’s slick, descending mancunt.

Derek ass dropped down. “Fuck, D. did you get bigger?”

Behind him Stiles laughed. “What’s in your ass, bitch? Tell us!”

“My alpha.” Derek gasped, rocking his hips experimentally forward. “My alpha’s dick. Stiles, watch me fuck it.” 

If it wasn’t for the cock ring’s binding Dustin thought he would have come again just hearing Derek say, “Only his cock can breed me.”

Dustin watched in awe as Derek began to raise and lower himself over the top of him. His hard rod slapped against his soft paunch with each thrust. He couldn’t believe how wet, hot and tight the silky side of alpha ass around his cock was. 

“Are you watching, Stiles? Are you seeing this man dick taking my fuck-cherry? FUCK! Fuck it’s stretching me.”

Derek’s tight sphincter clenched him rhythmically fighting the sensation of invasion. 

“Fuck, I feel so full,” Derek rumbled.

“You should,” Stiles teased, setting his hands on Derek’s hips to guide his up and down cadence. “That’s a solid five inches sinking in you right now, Der Bear.”

“Five and a half!” Dustin shouted, wanting to be sure every bit of him was counted.

“Fuck. Feels like twelve,” Derek grunted grinding his hips.

“That’s because it’s your first time.” Stiles rolled his eyes but his tone was playful, “Maybe now you’ll have a little more sympathy for me, Mr. Monster cock.” 

“I want to move,” Dustin broke in. “Can I fuck him missionary?”

“You heard the man, Der!” 

Before Stiles even finished his declaration Derek slipped off Dustin’s cock. There was a wet half fart/half squelch as his freshly fucked hole gasped, emptied for the moment. Derek immediately rolled over onto his back. His thick thighs lifted almost to his chest, the backs of them held up in his hands.

“Look at our bitch spread out for us, Dusty.” Stiles reached over and traced Derek’s hole. It was no baby gape now. Dustin could see deep inside him. Pride bloomed in his chest at what his cock had wrought.

“Alpha, I need you back in me.”

Dustin didn’t waste any time. He slid between Derek’s thighs and pushed in with one slow, hard thrust. He began pushing in and pulling almost out. The vision of his dick pumping into Derek’s fresh asshole put him in a trance. The way the ring of his sphincter stretched outward chasing the retreating slide of his dick…

His fan fiction sex scenes were about to get a hell of a lot better.

Stiles stretched out along Derek’s side. Dustin watched him take turns pinching Derek’s nipples.

“How’s it feel to have a man inside you, Babe? Splitting that tight alpha ass open.”

Dustin found Derek staring up at him, expression one of tortured bliss. “Fucking aches in the best way, Stiles… Feels. Good. Full….” 

He looked so impossibly gorgeous like this. On his back, splayed open. Dripping dick juddering against his flat, muscle bound belly. Balls hitching on every thrust.

“Dustin’s fucking you good, is he?”

Derek answered by letting go of his thighs. Dustin found himself encircled by impossibly strong legs. Cinched around his waist they held him tight and urged him in deeper.

“So good. Stiles,” Derek had finally found his voice it seemed. ‘UGH, Getting fucked feels so damn good!

“This dick... YES… Right there D. Your thick man dick is pounding me so fine. It’s going to breed me. YES. YES.”

“Oof… He’s getting loud, eh?” Stiles laughed.

Dustin agreed and decided to do something about it. He dropped down onto Derek’s torso, pinning Derek’s massive cock under the bulk of his belly. He wrapped his arms around Derek. His hands slipped under his back and gripped the tops of his shoulders. Derek wrapped his arms around Dustin as well. Fingernails lightly scratched at his back.

Derek stretched his mouth up and Dustin bent down to meet him. Their tongues tangled, Dustin’s no longer passive. His hips kicked up their pace as the familiar buzz built in his balls and tickled his dick letting him know he was getting close.

Derek broke their kiss. “Your cock feels so damn good.” He practically howled at the ceiling, “I love the way you split me open.” He tipped his head back, dark lashes fluttering. “After tonight I can’t ever say I’m only a top. Because you’ll have made me your bottom…”

As he said this his eyes rolled back into his head and he let out a guttural groan. Dustin felt Derek’s trapped cock spasm and the gush of sticky fluid between their sliding, sweat-slick skins.

“Did you come on that dick, slut? The very first time you have a cock in your ass, no less?” Stiles snorted. “I knew you’d be a natural!”

Above him there was a rapid clicking. Dustin looked up to see Stiles had pulled his phone from the pocket of his discarded coffee shop khakis and was snapping pictures.

“Hey, what can I say? I thought this was a moment worth commemorating. Something you might want to show your friends. How bout you flash me a little victory sign there Dusty. Let ‘em know you conquered that alpha man-cunt ” Stiles grinned at Dustin’s groan. “You close, man?”

Dusty nodded. 

“Let’s try one more thing, huh?”

The one more thing involved Derek laying flat on his belly, head between Stiles’ splayed thigh’s, mouth on his cock. Dusty watched Derek’s artful sucking from atop him, his own thighs straddling Derek hips. 

Derek deep-throated Stiles’ not insignificant eight-inches with the skill of a sword swallower. Seeing the size of his cock, Dustin could see why they might want to use a smaller “starter model” to break this ass in first.

His gaze shifted away from Derek and Stiles to himself, down to where his hands pushed the mounds of Derek’s ass together. His dripping cock slid between the lube-greased crack of fat cheeks. Dustin pulsed his hips rutting against Derek’s plump buttcheeks just like he did his favorite pillow.

With the cockring off and the sight of Derek’s broad alpha body lying so submissively beneath him, it didn’t take long to bring him to the brink.

“Remember to cum inside him,” Stiles reminded. “He needs that ass filled.” With a groan Stiles did his own filling, emptying his cock down Derek’s throat.

Dustin nodded, as the sight of Derek chugging down Stiles cum pushed him over the edge. The first jet of cum boiled out of his cock so hard and fast though it got away from him and shot high enough to catch the lower edge of Derek’s back tattoo.

Before he spent his whole wad, quickly grabbing handfuls of fat cheeks, Dustin spread Derek’s ass open one more time and plunged his jerking cock roughly into his still gaping hole.

“Oh, fuck, yes!” Derek had just slid off Stiles’ dick. Voice fuck-roughened he moaned into the mattress. “I can feel you filling me up, Breeding me… knock this alpha up, sweetheart.”

At that second needy “sweetheart,” Dustin came so hard his vision went blurry for a few seconds. He held himself deep in Derek’s cunt until his cock stopped twitching.

“Wait, don’t pull out yet!” 

Stiles popped up and darted around beside him, holding his phone again.

“Okay. Slowly,”

Dustin eased the blushed head of his deflating dick out of Derek’s broken in mancunt. Stiles snapped numerous photos. In one, he had Dustin smile and point to Derek’s leaking cream stuffed hole.

Stiles slid two fingers into Derek and pried him further open, watching Dustin’s cum drip out. “Nice work, Dusty. Hard to believe this was a virgin hole not even an hour ago.” Stiles handed Dustin his phone to take some photos of his own. Dustin’s first was Derek’s cum-dribbling, creampied hole next to his cock. 

Meanwhile, Stiles crawled back up to Derek and offered him his filthy fingers. Derek took them easily and sucked, his eyes heavy-lidded and sleepy-looking.

Stiles patted the space on the mattress next to him. Dustin, clambered over and curled up next to him.

“So, hey. There’s like still eight hours left of Valentine’s Day left. What do you say, we let the big guy here recover a bit. Then make him order us pizza.

“I’ve got all the Star Wars movies downloaded. We could have a film fest. And a fuck fest too, in between.” Stiles pulled his fingers from Derek’s lips and ran them through his dark sweaty bangs. “Cause I know now he’s experienced the joys of bottoming, Derek’s going to want to practice…”

**Notes for the Chapter:**

> Thank you for reading.


	6. BONUS BIT

**Summary for the Chapter:**

> The end...
> 
> Or the beginning?

The next morning Dustin was getting ready to go. Wearing a pair of Derek’s sweats and one of his tee-shirts he gathered up his own clothes into a plastic bag to take them home. 

Never in his life had he had such an amazing night. He laughed to himself at Stiles’ off key singing coming from the kitchen. His own heart matched its lightness. 

His hand reached down beside the bed for his soiled briefs from the night before, now stiff from the starch of dried jizz. 

Dustin started when a big hand covered his own. He looked up to see Derek crouched next to him. He had an uncomfortable blush building under his morning-manicured stubble.

“Uh… Don’t suppose you might ‘forget’ and leave these here?”

Seeing Dustin’s questioning expression Derek cleared his throat. “Ummm… as a reminder? I wouldn’t mind having a souvenir.

“You have your pillow and,” he confessed, “I… uh… I kind of collect smells...”

Dustin learned a lot about his own power over the course of the previous night. And, after numerous rounds of fucking, he was feeling the mantle of his recently realized manhood settling more comfortably.

He shot Derek a sly look.

“Maybe we could make a trade…”

Derek regarded him curiously. “What did you have in mind, D?”

* * *

Two weeks later Dustin arrived home at his apartment. Seeing the box on the doorstep he was glad his annoying roommates were out. Heart beating fast in his chest, he pulled the large package into his bedroom and shut the door behind him.

Cardboard flaps ripped open, he reached in and pulled out a new body pillow sheathed in opaque plastic. Sliding this back revealed Derek’s image, printed onto the washable pillow’s cover.

One side showed Derek’s front. Completely nude from head to shaven torso. Cut off just below the top third of his thick thighs, his hard cock jutted from his groin. The back of the pillow showed Derek from the back, peering over his shoulder, hands spreading his gorgeous ass cheeks to reveal his pucker. There was a special removable fleshlight sleeve mounted into the plush where Derek’s tight furl would be. 

Clutching the pillow to his chest, Dustin fondly remembered the rest of the morning after he and Derek struck their bargain, Derek sitting on his lap on the couch being fed bits of Stiles’ slightly burned pancakes from his chubby fingers. How Stiles watched and encouraged Derek to lick all the syrup from them.

Eyes clearing, cock hardening, Dustin glanced into the pillow box and noticed an envelope on its bottom. He tucked the pillow under his arm, pulled the envelope out, and opened it. Inside, was another printed picture of Derek’s ass. This time with a rainbow body-painted over one cheek and a black arrow sharpie tramp stamp pointing down between his ass cheeks. “Pot ‘o Gold” written over the arrow, 

At the bottom of the picture in Stiles’ scritchy writing was a second invitation from his favorite couple. This one for a St. Patrick’s day “celebration.”

  
  
  


**Notes for the Chapter:**

> Thank you for reading.


End file.
